JP2002338649A - Catalyst for producing polyurethane resin and method for producing polyurethane resin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing a polyurethane resin which can give a product with good production and moldability and baraly leaves an amine in the product to free from; and a catalyst for use in the same. SOLUTION: The method for producing a polyurethane resin comprises using an amine compound as the catalyst, wherein the amine compound is comprised of a compound represented by formula (1) (wherein R<1> and R<2> are each independently a 1-4C alkyl group, and A is a 5-10C straight or branched alkylene group).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a catalyst for producing a polyurethane resin such as soft, hard, semi-hard, elastomer, etc.
And a method for producing a polyurethane resin or a polyurethane foam using the same. More particularly, it relates to a catalyst and a method for producing a polyurethane resin or a polyurethane foam which emits little volatile amine.

[0002]

2. Description of the Related Art Polyurethane resins are produced by reacting a polyol and an organic polyisocyanate in the presence of a catalyst and, if necessary, a foaming agent, a surfactant, a crosslinking agent and the like.
Conventionally, it has been known to use a large number of metal compounds and tertiary amine compounds as catalysts in the production of this polyurethane resin. These catalysts are widely used industrially either alone or in combination.

In particular, tertiary amine compounds are widely used as tertiary amine catalysts for producing polyurethane resins because of their excellent productivity and moldability. For example, conventionally known triethylenediamine, N, N, N ′, N′-tetramethyl-1,6-hexanediamine, bis (2-dimethylaminoethyl) ether, N, N, N ′, N ″,
Compounds such as N "-pentamethyldiethylenetriamine, N-methylmorpholine, N-ethylmorpholine, and N, N-dimethylethanolamine.

[0004] Metal-based catalysts are often used in combination with tertiary amine catalysts in many cases because of poor productivity and moldability, and are rarely used alone.

[0005]

However, the above-mentioned tertiary amine catalysts remain in free form in polyurethane resin products and cause various problems because they are gradually discharged as volatile amines. For example, the odor problem of volatile amines emitted from polyurethane foam products in automobiles. Further, in recent years, a so-called fogging problem has occurred in which volatile components in a polyurethane foam have adhered to a window glass of an automobile, causing fogging of the window glass and reducing commercial value. Another problem is the contamination of other materials by volatile amines emitted from polyurethane products.

For these volatile tertiary amine catalysts,
As a method for solving this problem, there has been proposed a method using an amine catalyst having a primary and secondary amino group or hydroxyalkyl group capable of reacting with an organic polyisocyanate in the molecule (Japanese Patent Laid-Open No. 46-4846). JP-A-59-191743, JP-B-61-31727, JP-B-57-14762, etc.). These amine catalysts are said to be immobilized in the polyurethane resin skeleton in the form of a reaction with the organic polyisocyanate, so that the above problem can be avoided. However, when an amine catalyst having these reactive groups is used, another problem occurs. Occurs.

That is, in general, an amine catalyst having a reactive group is immobilized in a polyurethane resin, so that the catalytic activity is greatly reduced and the curing of the polyurethane resin is insufficient. As a result, the productivity is reduced. In addition, most of the amine catalysts having these reactive groups are incompletely reacted and remain free in polyurethane resin products, and are gradually discharged as volatile amines. Further, there are some which once react with the organic polyisocyanate and are fixed in the polyurethane resin skeleton, but when the temperature inside the vehicle becomes high, the bond is decomposed and the amine is discharged as free amine.

Further, metal catalysts other than amine-based catalysts, such as organotin compounds, do not cause the above-mentioned problems, but their use alone deteriorates productivity, physical properties and moldability, and environmental problems due to tin have been reported. I have.

The present invention has been made in view of the above problems, and an object of the present invention is to provide a method for producing a polyurethane resin having almost no amine discharged from a product with good productivity and moldability, and a catalyst used therefor. It is to provide.

[0010]

Means for Solving the Problems The present inventors have made intensive studies to solve the above problems. As a result, an amine compound containing one primary amino group and one tertiary amino group in the molecule and having 5 to 10 carbon atoms in the alkyl group between both amino groups is used as an amine catalyst in the production of the polyurethane resin. It was found that the use of the compound produced almost no volatile amine, did not decompose the bond, and that the polyurethane resin could be obtained with good moldability and productivity, and completed the present invention.

That is, the present invention is a catalyst for producing a polyurethane resin comprising an amine compound represented by the following general formula (1), and a method for producing a polyurethane resin or a polyurethane foam using the catalyst as a catalyst.

[0012]

Embedded image (In the above formula, R ¹ and R ² each independently represent an alkyl group having 1 to 4 carbon atoms, and A represents a linear or branched 5 to 10 carbon atoms.
Represents an alkylene group. Hereinafter, the present invention will be described in detail.

The catalyst for producing a polyurethane resin of the present invention is an amine compound represented by the above general formula (1).

In the present invention, the amine compound of the general formula (1) contains one primary amino group and one tertiary amino group in the molecule, and the alkyl group between both amino groups has 5 to 5 carbon atoms.
It is 10. The number of carbon atoms is preferably 5 to 8 from the viewpoints of the residual amount of amine in the urethane resin and the catalytic activity, and particularly preferable are 5 and 6 carbon atoms.

By the way, it has been proposed to use dialkyl-substituted primary amines such as dimethylaminopropylamine and diethylaminoethylamine as catalysts for producing polyurethane foam (JP-A-46-4846).
No.).

However, in this method, as with the conventional volatile tertiary amines, there is a problem of odor and toxicity, and further, there is a problem that the flowability at the time of foaming is poor and the reactants are not filled in every corner of the mold. (JP-A-59-1917)
No. 43).

For this reason, Japanese Patent Application Laid-Open No. Sho 59-191743 discloses that such a dialkyl-substituted primary amine is converted to a carbonate to form a problem as described in Japanese Patent Application Laid-Open No. 46-4846. Is going to be resolved.

For example, a primary amino group (—N
Since all the catalyst molecules have H ₂ ) and react with isocyanate groups and are chemically bonded to the polymer skeleton, no odor is generated upon demolding. Examples of the alkylene group in the dialkyl-substituted primary amines include ethylene and n.
-Propylene and n-butylene groups are preferred from the viewpoint of catalytic activity.

However, as a result of the study by the present inventors,
The carbonates of dialkyl-substituted primary amines having an ethylene, n-propylene or n-butylene group as an alkylene group, which are preferred in JP-A-59-191743, have low catalytic activity and are useful in polyurethane resin production. It became clear that the productivity was low and the moldability deteriorated. Further, it was also found that as the number of carbon atoms in the alkylene group increases, the dialkyl-substituted primary amines remain in the urethane resin in a large amount in a free form, which significantly deteriorates the odor of the foam.

On the other hand, the amine compound represented by the above general formula (1) of the present invention specifically has a high catalytic activity, remarkably improves the productivity and moldability, and has a free form in the urethane resin. The present inventors have found that a foam having a low amine odor can be obtained since only a small amount remains in the foam. As is clear from the above, the present invention has a special effect which cannot be expected at all from these prior arts.

The amine compound of the present invention includes N, N-
Dimethylpentamethylenediamine, N, N-dimethylhexamethylenediamine, N, N-dimethylheptamethylenediamine, N, N-dimethyloctamethylenediamine, N, N-dimethylnonamethylenediamine, N, N-
Dimethyldecamethylenediamine, N, N-diethylpentamethylenediamine, N, N-diethylhexamethylenediamine, N, N-diethylheptamethylenediamine,
N, N-diethyloctamethylenediamine, N, N-diethylnonamethylenediamine, N, N-diethyldecamethylenediamine, N, N-dipropylpentamethylenediamine, N, N-dipropylhexamethylenediamine,
N, N-dipropylheptamethylenediamine, N, N-
Dipropyloctamethylenediamine, N, N-dipropylnonamethylenediamine, N, N-dipropyldecamethylenediamine, N, N-dibutylpentamethylenediamine, N, N-dibutylhexamethylenediamine, N, N
-Dibutylheptamethylenediamine, N, N-dibutyloctamethylenediamine, N, N-dibutylnonamethylenediamine, N, N-dibutyldecamethylenediamine and the like. N, N-dimethylpentamethylenediamine and N, N-dimethylhexamethylenediamine have high catalytic activity and are more preferable.

The amine compound represented by the general formula (1), which is the catalyst of the present invention, can be easily produced by a method known in the literature. For example, a method of reacting a dialkylamine with a bromoalkyl-N-phthalimide obtained by reacting a dialkylaminoalkanol and ammonia with a reductive amination reaction of ammonia or an alkyldibromide with potassium phthalimide in the presence of an excess of alkyldibromide and then reacting hydrazine. No.

Usually, when the catalyst of the present invention is used for the production of a polyurethane resin, the amount of the polyol used is 1
When the amount is 00 parts by weight, it is 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight. If a large amount of the catalyst is used, the productivity of the polyurethane resin is improved, but the amount of the volatile amine is undesirably increased.

The catalyst of the present invention reacts with polyisocyanate, which is a raw material of polyurethane resin, and is fixed in the polyurethane resin skeleton. Further, the immobilized catalyst of the present invention does not decompose even when exposed to high temperatures. Therefore, the catalyst of the present invention hardly exists as a free amine in the polyurethane resin, and no volatile amine comes out. That is, in the polyurethane resin product using the catalyst of the present invention, it is possible to prevent the various problems described above, for example, the odor and fogging due to the volatile amine.

The process for producing a polyurethane resin using the catalyst according to the present invention comprises reacting a polyol with an organic polyisocyanate in the presence of a catalyst and, if necessary, a foaming agent, a surfactant, a crosslinking agent and the like. Is a way to get Examples of the product include a flexible polyurethane foam, a semi-rigid polyurethane foam, and a rigid polyurethane foam produced using a foaming agent, and an elastomer product not using a foaming agent. Among these, it is preferably applied to a flexible polyurethane foam, a semi-rigid polyurethane foam and a rigid polyurethane foam produced using a foaming agent.

The polyurethane resin produced according to the present invention contains a volatile amine catalyst in an amount of 300 / g of polyurethane resin.
less than 100 μg due to environmental problems in automobiles
/ G or less is more preferred. The volatile amine catalyst amount indicates the total amount of amine catalyst generated from the polyurethane resin when the polyurethane resin is heated at 65 ° C. for 48 hours in a methanol solvent.

As the polyol used in the method for producing a polyurethane resin of the present invention, conventionally known polyether polyols, polyester polyols, polymer polyols, and flame-retardant polyols such as phosphorus-containing polyols and halogen-containing polyols can be used. . These polyols can be used alone, or can be used by being appropriately mixed and used in combination.

Examples of the polyether polyol include polyhydric alcohols such as ethylene glycol, propylene glycol, glycerin, trimethylolpropane and pentaerythritol, amines such as ethylenediamine, and alkanolamines such as ethanolamine and diethanolamine. A compound having at least two or more active hydrogen groups such as, for example, is used as a starting material, and an alkylene oxide typified by ethylene oxide or propylene oxide is added thereto.
"Polyurethan"
e Handbook "(1985 edition) Hanse
r Publishers (Germany), pp. 42-53.

Examples of the polyester polyol include those obtained from the reaction of dibasic acid and glycol, and those described in Keiji Iwata, "Polyurethane Resin Handbook" (First Edition, 1987), Nikkan Kogyo Shimbun, page 117. Examples of the waste include nylon waste, TMP, pentaerythritol waste, phthalate-based polyester waste, and polyester polyols obtained by treating and deriving waste.

Examples of the polymer polyol include a polymer polyol obtained by reacting the polyether polyol with an ethylenically unsaturated monomer such as butadiene, acrylonitrile, and styrene in the presence of a radical polymerization catalyst.

Examples of the flame-retardant polyol include a phosphorus-containing polyol obtained by adding an alkylene oxide to a phosphoric acid compound, a halogen-containing polyol obtained by ring-opening polymerization of epichlorohydrin or trichlorobutylene oxide,
Phenol polyol and the like can be mentioned.

The molecular weight of these polyols is from 62 to 150.
00 can be used. As the flexible polyurethane foam, those having a molecular weight of 1,000 to 15,000 are used, and polyether polyols and polymer polyols having a molecular weight of 3,000 to 15,000 are preferred. More preferred is a flexible polyurethane foam used in combination with a polyether polyol and a polymer polyol.

The organic polyisocyanate used in the present invention may be any known one, for example, aromatic polyisocyanates such as toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), naphthylene diisocyanate and xylylene diisocyanate;
Examples thereof include aliphatic polyisocyanates such as hexamethylene diisocyanate, alicyclic polyisocyanates such as dicyclohexyl diisocyanate, and isophorone diisocyanate, and mixtures thereof. TDI and its derivatives include 2,4-toluene diisocyanate and 2,6-toluene
Mention may be made of mixtures of toluene diisocyanates or terminal isocyanate prepolymer derivatives of TDI. Examples of MDI and its derivatives include a mixture of MDI and its polymer, polyphenyl-polymethylene diisocyanate, and / or a diphenylmethane diisocyanate derivative having a terminal isocyanate group.
Of these organic polyisocyanates, TDI and MDI are preferably used.

The use ratio of the organic polyisocyanate and the polyol is not particularly limited, but is generally represented by a soft foam or a semi-rigid foam in terms of isocyanate index (isocyanate group / active hydrogen group capable of reacting with isocyanate group). Is generally 60
From 130 to 130, and generally from 60 to 400 in the production of rigid foams and urethane elastomers.

The catalyst used in the method for producing a polyurethane of the present invention is the above-mentioned catalyst of the present invention, but other catalysts can be used in combination without departing from the present invention. Other catalysts include, for example, conventionally known organic metal catalysts, tertiary amines and quaternary ammonium salts.

Examples of the organometallic catalyst include stannas diacetate, stannas dioctoate, stannas dioleate, stannas dilaurate, dibutyl tin oxide, dibutyl tin diacetate, dibutyl tin dilaurate, dibutyl tin dichloride, dioctyl tin dilaurate, octane Lead acid, lead naphthenate, nickel naphthenate, cobalt naphthenate and the like. The tertiary amines may be any of conventionally known ones, for example,
N, N, N ', N'-tetramethylethylenediamine,
N, N, N ', N'-tetramethylpropylenediamine, N, N, N', N ", N" -pentamethyldiethylenetriamine, N, N, N ', N ", N" -pentamethyl- (3- Aminopropyl) ethylenediamine, N,
N, N ', N ", N" -pentamethyldipropylenetriamine, N, N, N', N'-tetramethylguanidine, 1,3,5-tris (N, N-dimethylaminopropyl) hexahydro-S -Triazine, 1,8-diazabicyclo [5.4.0] undecene-7, triethylenediamine, N, N, N ', N'-tetramethylhexamethylenediamine, N-methyl-N'-(2-dimethylamino Ethyl) piperazine, N, N'-dimethylpiperazine, dimethylcyclohexylamine, N-methylmorpholine, N-ethylmorpholine, bis (2-dimethylaminoethyl) ether, 1-methylimidazole, 1,2
Tertiary amine compounds such as -dimethylimidazole, 1-isobutyl-2-methylimidazole and 1-dimethylaminopropylimidazole. Also, tertiary amine compounds having a reactive group other than the present invention can be used. For example, dimethylethanolamine, dimethylisopropanolamine, N, N-dimethylhexanolamine, dimethylaminoethoxyethanol, N, N-dimethyl-N '-(2-hydroxyethyl) ethylenediamine, N, N-dimethyl-N'-(2-hydroxyethyl) propanediamine, N-methyl-N '-(2-hydroxyethyl) piperazine, bis (dimethylaminopropyl) amine , Bis (dimethylaminopropyl) isopropanolamine, 1- (2-hydroxyethyl) imidazole, 1- (2-hydroxypropyl) imidazole, 1- (2-hydroxyethyl) -2-methylimidazole, 1- (2-hydroxy Propyl) -2-methylimidazole 3-quinuclidinol, and the like.
Examples of the quaternary ammonium salts include conventionally known tetraalkylammonium halides such as tetramethylammonium chloride, tetraalkylammonium hydroxides such as tetramethylammonium hydroxide, tetramethylammonium 2-ethylhexanoate, Tetraalkylammonium organic acid salts such as hydroxypropyltrimethylammonium formate and 2-hydroxypropyltrimethylammonium 2-ethylhexanoate are exemplified.

The blowing agent used in the method for producing a polyurethane resin of the present invention is water and a low-boiling organic compound. The low-boiling organic compound is a hydrocarbon-based or halogenated hydrocarbon-based compound. Known hydrocarbons include methane, ethane, propane, butane, pentane, hexane and the like. Examples of the halogenated hydrocarbon include known halogenated methane, halogenated ethanes, and fluorinated hydrocarbons such as methylene chloride, HCFC-141b, and HF.
C-245fa, HFC-356mfc and the like can be used. In using these foaming agents, water and a low-boiling organic compound may be used alone or in combination. A particularly preferred blowing agent is water. The amount used may vary depending on the density of the target product, but is usually 0.1 part by weight or more, preferably 0.5 to 10.0 parts by weight, per 100 parts by weight of the polyol.

If necessary, a surfactant can be used in the present invention. The surfactant used in the present invention is a conventionally known organosilicone surfactant, and its amount is 0.1 to 10 parts by weight based on 100 parts by weight of the polyol.

In the present invention, if necessary, a crosslinking agent or a chain extender can be added. As a crosslinking agent or a chain extender, a low molecular weight polyhydric alcohol, for example,
Examples thereof include low molecular weight amine polyols such as ethylene glycol, 1,4-butanediol, and glycerin, such as diethanolamine and triethanolamine, and polyamines such as ethylenediamine, xylylenediamine, and methylenebisorthochloroaniline. Of these, diethanolamine and triethanolamine are preferred.

In the present invention, if necessary, a coloring agent,
Flame retardants, antioxidants and other known additives can also be used. The types and amounts of these additives can be used in a range usually used as long as they do not deviate from known types and procedures.

The product produced by the method for producing a polyurethane resin of the present invention can be used for various purposes. For flexible foams, for example, beds as cushions, car seats, mattresses, etc. For semi-rigid foam, for example, instrument panels, headrests, steering wheels, etc. related to automobiles. For rigid foams, for example, freezers, refrigerators, insulation materials, etc. For elastomer products, for example, adhesives, flooring,
Waterproof materials and the like can be mentioned.

Hereinafter, the present invention will be described based on examples and comparative examples, but the present invention is not limited to these examples.

Examples 1 to 4, Comparative Examples 1 to 1
1 shows an example in which a flexible and highly elastic polyurethane foam was produced using the catalyst of the present invention and the catalyst of the comparative example.

N, N-dimethylpentamethylenediamine, N, N-dimethylhexamethylenediamine, N, N
-Dimethyloctamethylenediamine and N, N-dimethyldecamethylenediamine were used as the catalyst of the present invention.

A premix A was prepared by mixing the polyol, water, crosslinking agent, and foam stabilizer at the raw material mixing ratios shown in Table 2. 86.6 g of Premix A was placed in a 300 ml polyethylene cup, and the catalyst of the present invention and the catalyst of Comparative Example shown in Table 1 were added in amounts of 60 seconds in the following gel time, and the temperature was adjusted to 20 ° C. . A polyisocyanate solution (TM80) whose temperature was adjusted to 20 ° C. in a separate container was mixed with an isocyanate index ｛isocyanate group / OH group (molar ratio).
× 100) Put into the cup of Premix A by an amount such that １０５ becomes 105, and quickly use a stirrer at 6000 rpm for 5 minutes.
Stirred for seconds. The mixed solution that had been mixed and stirred was transferred to a 2 liter polyethylene cup whose temperature was adjusted to 50 ° C., and the reactivity during foaming was measured. Next, the scale of the raw material was increased, and the temperature was adjusted to 50 ° C. by the same operation (inner dimensions, 35 × 35 ×
10cm aluminum) with a total foam density of 45kg /
The mixture was filled so as to obtain m ^3, and a lid was formed to perform foam molding. The foam was demolded 5 minutes after the time when the mixed solution was put. From molding foam to foam formability, cure,
The total density of the foam, the core density, the amount of amine catalyst volatilized and the odor of the foam were measured and compared. Table 3 shows the results.

[0046]

[Table 1]

[Table 2]

[Table 3] In addition, the measuring method of each measurement item is as follows.

Reactivity measurement items Cream time: foaming start time, time to start rising of foam are visually measured Gel time: time to progress from reaction to change from liquid material to resinous material Rise time: foam time The time at which the ascent stops is measured visually.

Formability of foam: Cell roughness on the surface of the molded foam was visually observed and evaluated as moldability as follows: ：: No cell roughness ○: Partial cell roughness △: Cell roughness is about half of the surface portion. ×: Cell roughness is present on the entire surface.

· Cure property of foam: 3 immediately after removal from mold
Put a weight of about 2kg on the foam for 5 seconds every 0 seconds,
The time when the dent on the foam did not remain was recorded (measurement of curing speed), and the curability was evaluated as follows. ：: The dent disappearing time was within 6 minutes. ：: The dent disappearing time was 6 to 8 minutes. Elapsed time is 8 minutes or more.

Form core density: The center of the molded foam was cut into a size of 20 × 20 × 5 cm, and the size and weight were measured accurately to calculate the core density.

Amine catalyst remaining amount: The amount of the amine catalyst in the foam was extracted by heating with a methanol solvent. That is, 1.5 ×
A foam of 1.5 × 5 cm size is cut, placed in a 20 ml pressure vessel together with methanol, and capped. This container is 6
It was left in an oven at 5 ° C. for 48 hours. After 48 hours, after confirming that there was no change in the weight of the container, the amine catalyst was quantified by gas chromatography. The quantitative value was expressed in μg of the amine catalyst per 1 g of the foam.

Odor of foam: A foam having a size of 5 × 5 × 5 cm was cut from the foam from which the foam core density was measured, placed in a mayonnaise bottle, covered, and then smelled by a monitor of 10 persons. ：: Almost no odor △: Slight odor ×: Strong odor

In Examples 1 to 4, the polyurethane foam using the catalyst of the present invention was prepared using a volatile amine catalyst containing 3
Since it is as small as 00 μg / g or less, the amine odor of the foam is small. In particular, in Examples 1 and 2, the foam does not have any amine odor since almost no amine catalyst remains. In addition, the catalytic activity is extremely high. In addition, the formability and cureability of the foam are good, and contribute to the productivity of the foam.

On the other hand, Comparative Examples 1 and 2 are examples of tertiary amine catalysts having no reactive group in the molecule, but because a large amount of volatile amine catalyst remains in the foam. The foam has a strong odor.

Comparative Example 3 is an example of an amine catalyst having a hydroxyethyl group in the molecule, but the foam has a strong odor because a large amount of volatile amine catalyst remains in the foam.

Comparative Example 4 is an example of an amine catalyst having a reactive secondary amino group in the molecule. The foam has a strong odor because a large amount of volatile amine catalyst remains in the foam.

Comparative Examples 5 and 6 are examples of amine catalysts having a short carbon chain having a reactive primary amino group in the molecule, but the volatile amine catalyst remained almost at 20 μg / g or less. The polyurethane foam has no amine odor. However, since the catalytic activity is low, a large number of parts are required, and the physical properties of the foam are remarkably reduced. In addition, the productivity of the foam is inferior due to poor moldability and cure properties of the foam.

Comparative Example 7 is an example of an amine catalyst having a long carbon chain having a reactive primary amino group in the molecule. However, since a volatile amine catalyst remains in the foam in a large amount, it is strong against the foam. I smell. In addition, a low catalytic activity requires a large number of copies.

Comparative Examples 8 to 10 are examples of amine carbonate catalysts having a reactive primary amino group in the molecule. However, since a large amount of volatile amine catalyst remains in the foam, The foam has a strong odor. Further, a low catalytic activity requires a large number of parts to be used.

Comparative Example 11 is an example of an amine carbonate catalyst having a reactive primary amino group in the molecule in which the amount of amine was adjusted to the same amount as in Example 2. And the foam has an amine odor due to a small amount of volatile amine catalyst remaining in the foam.

[0061]

According to the catalyst of the present invention, a polyisocyanate as a raw material of a polyurethane resin reacts with a primary amino group,
Since it is fixed in the polyurethane resin skeleton and the catalyst does not migrate to the resin surface or the like, it is effective for preventing PVC discoloration of the automobile instrument panel due to the migration of the catalyst and for preventing the fogging phenomenon of the window glass due to the migration of volatile components from the foam. Also, the odor of the produced foam is reduced, which greatly contributes to improving the environment at the foaming site. Furthermore, soft, hard, semi-hard,
It is extremely effective in producing polyurethane such as elastomer.

Continued on the front page F-term (reference) 4J034 BA03 DA01 DB03 DB04 DB07 DC02 DC50 DF01 DG02 DG03 DG04 DG22 DG28 DG29 DQ01 DQ05 DQ09 DQ16 DQ18 HA01 HC03 HC12 HC13 HC22 HC64 HC71 KA01 KB02 KC17 KC18 KC35 NA12 Q01 NA01

Claims (3)

[Claims] 1. A catalyst for producing a polyurethane resin comprising an amine compound represented by the following general formula (1). Embedded image (In the above formula, R ¹ and R ² each independently represent an alkyl group having 1 to 4 carbon atoms, and A represents a linear or branched 5 to 10 carbon atoms.
Represents an alkylene group. ) 2. A method for producing a polyurethane resin, comprising reacting a polyol with an organic polyisocyanate in the presence of the catalyst according to claim 1. 3. A method for producing a polyurethane foam, comprising reacting a polyol with an organic polyisocyanate in the presence of the catalyst according to claim 1 using water and a low-boiling organic compound as a blowing agent.